Yea, for the Aspire resort credit, it doesn't matter who's name the reservation is under or how many different reservations you have or anything like that. All that matters is that a charge from an eligible hotel posts to your Aspire card. At check-out, just have the hotel charge $250 to one Aspire and the balance to the other Aspire, as matrixwalker2012 mentioned above. This will be no problem.

Long running wiki thread on the Hilton forum with FAQ:

https://www.flyertalk.com/forum/hilt...rt-credit.html